How many flights from Chicago to Punta Cana are non-stop?

Historically, approximately 6.5% of flights from Chicago to Punta Cana were non-stop. For travelers with connecting flights, the median number of stopovers was typically 2. This data reflects observations over a 90-day period. The majority of available options for this route historically involved at least one stop.

How many hours is the flight from Chicago to Punta Cana?

The typical direct flight from Chicago to Punta Cana has a median duration of 4 hours and 45 minutes. For flights with one stop, the median travel time historically extended to 11 hours and 19 minutes. The direct distance covered by this route is approximately 3192 kilometers. Travelers should anticipate a significantly longer journey if their itinerary includes a layover.

Are there frequently good prices on flights from Chicago to Punta Cana?

Historically, good prices on flights from Chicago to Punta Cana have been frequent. This route is classified as one with consistent deal availability. Travelers looking for value on this route have typically found opportunities across the trailing quarter. This assessment is based on observations over a 30-day period.

Flights From Chicago

To Punta Cana

Cheap Flights from Chicago to Punta Cana

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Punta Cana

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)

Today’s best flight deals from Chicago to Punta Cana

Explore current cheapest deals departing from Chicago to Punta Cana

2027-04-19 – 2027-04-25
CHI - Punta Cana
67% AI deal score
$344
$349
Round trip
2027-04-23 – 2027-04-25
CHI - Punta Cana
70% AI deal score
$371
$349
Round trip
2027-04-12 – 2027-04-25
CHI - Punta Cana
67% AI deal score
$331
$349
Round trip
2027-04-24 – 2027-04-25
CHI - Punta Cana
70% AI deal score
$373
$349
Round trip
2027-01-25 – 2027-02-06
CHI - Punta Cana
66% AI deal score
$269
$363
Round trip
2027-01-29 – 2027-02-06
CHI - Punta Cana
66% AI deal score
$282
$369
Round trip
2027-04-09 – 2027-04-11
CHI - Punta Cana
67% AI deal score
$356
$369
Round trip
2027-04-05 – 2027-04-25
CHI - Punta Cana
67% AI deal score
$325
$369
Round trip
2027-04-05 – 2027-04-11
CHI - Punta Cana
67% AI deal score
$344
$369
Round trip
2027-04-09 – 2027-04-25
CHI - Punta Cana
67% AI deal score
$329
$369
Round trip

Chicago to Punta Cana: Overview

Insights for flights from Chicago to Punta Cana

A typical journey from Chicago to Punta Cana, including connections, takes about 4h 45m. This route is classified as medium-haul, covering a distance of 3192 kilometers. Given that most itineraries involve connections, the overall travel time can vary significantly depending on the number and duration of layovers.

For travelers looking for cheap flights from Chicago to Punta Cana, fares typically range from $666–$1216, with a median price of $905. Right now, current fares are near the typical level for this route. New deals for this route appear almost daily, suggesting frequent opportunities to find competitive prices.

When considering the cheapest time to fly from Chicago to Punta Cana, June stands out with a median fare of $445. April also offers more affordable options, with a median fare of $548. Another favorable month for lower prices is October, where the median fare is $670.

Most itineraries from Chicago to Punta Cana involve connections, with only 6.5% of recent fares being non-stop. For connecting flights, the typical number of stopovers is 2. This means that if you fly this route, you will likely have at least two stops before reaching your destination.

How much is a round trip from Chicago to Punta Cana

Regular price: $252 - $614

Prices for flights from Chicago to Punta Cana are currently within the regular range.

The regular price range for flights from Chicago to Punta Cana is typically between $252 and $614. The current lowest deal is $343 with Maersk Air, for travel from Jan 18-Jan 24.

now $343

Low $252

High $614

The cheapest time to fly from Chicago to Punta Cana

The cheapest month to fly from Chicago to Punta Cana is June, with a median price of $445. The most expensive month is December, with a median price of $1408. Prices are generally lower from January to November.

June

Cheapest

Flights from $445

December

Most Expensive

Flights from $1,408

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Punta Cana

Maersk Air

Last-minute flights going from Chicago to Punta Cana

Fri, Nov 13

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$388

$386

One-way

Sat, Nov 14

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$388

$386

One-way

Sat, Nov 14

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Swiss International Air Lines

$467

$11,960

One-way

Sun, Nov 29

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Swiss International Air Lines

$430

$11,907

One-way

Mon, Nov 30

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$411

$389

One-way

Mon, Nov 30

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$353

$392

One-way

Biggest price drops on these dates for flights from Chicago to Punta Cana

3 nights

Nov 15 - Nov 18

$494 → $419

15%

3 nights

Nov 3 - Nov 6

$480 → $425

11%

7 nights

Nov 10 - Nov 17

$468 → $419

10%

5 nights

Dec 7 - Dec 12

$448 → $400

11%

Popular Airports to fly from Chicago to Punta Cana

Chicago - Punta Cana route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from Chicago to Punta Cana are near the typical level for this route.

📅 Best time to fly

Fly in June for prices as low as $445

Historically, June is the cheapest month to fly, with a median price of $445.

⏱️ Flight duration

Direct flights take 4h 45m

The median flight time for a direct flight to Punta Cana is 4h 45m.

✈️ Airlines & availability

Connecting flights are dominant

Only 6.5% of recent flights from Chicago to Punta Cana are direct.

🏆 Airline highlight

Maersk Air offers direct flights

Maersk Air is one airline that has offered direct flights on this route recently.

🎯 Booking tip

Deals appear frequently

Deals on flights from Chicago to Punta Cana appear frequently, about every 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers flights to Punta Cana, with prices starting from $314, making it a budget-friendly option.

📍 ~25 km from Chicago (reachable by car or train)

💸 Flights from ~$314

Chicago Midway International (MDW)

Chicago Midway International provides another option for flights to Punta Cana, with prices from $435.

📍 ~14 km from Chicago (reachable by car or train)

💸 Flights from ~$435

Chicago Rockford International (RFD)

Chicago Rockford International offers an alternative departure point for flights to Punta Cana, with prices from $431.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$431

Punta Cana main airports to arrive at

Punta Cana International (PUJ)

Cheapest

Punta Cana International Airport is a convenient arrival point for your trip to Punta Cana.

📍 ~5 km from Punta Cana (reachable by car)

💸 Flights from ~$323

Airports nearby Punta Cana used as alternative

La Romana International (LRM)

La Romana International is the closest alternative airport, located within an hour's drive via the Coral Highway.

📍 ~70 km from Punta Cana (reachable by car)

💸 Flights from ~$911

Business & First Class Flight Deals to Punta Cana

Discover luxury on the budget with premium cabin class on flights from Chicago to Punta Cana.

Elite

Best Elite deals to Punta Cana

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Oct 28

Punta Cana, Dominican Republic

85% AI deal score

$2,043

$1,245

Save $798

Copa Airlines

Business Class

From ORD

Elite

Oct 31

Punta Cana, Dominican Republic

85% AI deal score

$1,998

$1,245

Save $753

Copa Airlines

Business Class

From ORD

Elite

Oct 28

Punta Cana, Dominican Republic

84% AI deal score

$1,891

$1,245

Save $646

Copa Airlines

Business Class

From ORD

Elite

Oct 28

Punta Cana, Dominican Republic

83% AI deal score

$2,091

$1,383

Save $708

Copa Airlines

Business Class

From ORD

Elite

Oct 30

Punta Cana, Dominican Republic

77% AI deal score

$2,073

$1,447

Save $626

Air Canada

Business Class

From ORD

Elite

Oct 30

Punta Cana, Dominican Republic

77% AI deal score

$1,954

$1,447

Save $507

Air Canada

Business Class

From ORD

Elite

Oct 27

Punta Cana, Dominican Republic

77% AI deal score

$2,060

$1,452

Save $608

Air Canada

Business Class

From ORD

Elite

Oct 29

Punta Cana, Dominican Republic

77% AI deal score

$2,075

$1,456

Save $619

Air Canada

Business Class

From ORD

Elite

Oct 31

Punta Cana, Dominican Republic

76% AI deal score

$1,942

$1,517

Save $425

Copa Airlines

Business Class

From ORD

Elite

Oct 28

Punta Cana, Dominican Republic

76% AI deal score

$2,107

$1,597

Save $510

Air Canada

Business Class

From ORD

Elite

Dec 07

Punta Cana, Dominican Republic

75% AI deal score

$1,828

$1,481

Save $347

Avianca

Business Class

From ORD

Elite

Oct 28

Punta Cana, Dominican Republic

75% AI deal score

$1,897

$1,518

Save $379

Copa Airlines

Business Class

Frequently Asked Questions About Flights to Punta Cana

Historically, the optimal booking window for flights from Chicago to Punta Cana is typically 28-59 days before departure. During this period, the average price observed was around $852. Prices tend to increase significantly for bookings made closer to the travel date, with fares averaging $1204 for tickets purchased 0-6 days out. Even bookings made 60+ days in advance were historically higher, averaging $1083.

Across the trailing quarter, a good price for a flight from Chicago to Punta Cana was considered to be $666 or less. The median price for this route historically stood at $905. Fares exceeding $1216 were typically in the higher price range. These figures are based on observations over a 90-day period.

Historically, the cheapest months to fly from Chicago to Punta Cana include June, with a median price of $445, and April, with a median price of $548. October also presented a relatively lower median price of $670. These prices are notably lower than the annual median price of $905 for this route, based on data collected over a 270-day window.

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More routes from Chicago

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Flights to Punta Cana from other cities

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Chicago to Punta Cana: Overview

Insights for flights from Chicago to Punta Cana

How much is a round trip from Chicago to Punta Cana

Regular price: $252 - $614

Prices for flights from Chicago to Punta Cana are currently within the regular range.

The regular price range for flights from Chicago to Punta Cana is typically between $252 and $614. The current lowest deal is $343 with Maersk Air, for travel from Jan 18-Jan 24.

now $343

Low $252

High $614

The cheapest time to fly from Chicago to Punta Cana

June

Cheapest

Flights from $445

December

Most Expensive

Flights from $1,408

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Punta Cana

Maersk Air

Last-minute flights going from Chicago to Punta Cana

Fri, Nov 13

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$388

$386

One-way

Sat, Nov 14

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$388

$386

One-way

Sat, Nov 14

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Swiss International Air Lines

$467

$11,960

One-way

Sun, Nov 29

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Swiss International Air Lines

$430

$11,907

One-way

Mon, Nov 30

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$411

$389

One-way

Mon, Nov 30

⌛ Last-Minute

ORD - Punta Cana

Chicago (ORD) - Punta Cana (PUJ)

Maersk Air

$353

$392

One-way

Biggest price drops on these dates for flights from Chicago to Punta Cana

3 nights

Nov 15 - Nov 18

$494 → $419

15%

3 nights

Nov 3 - Nov 6

$480 → $425

11%

7 nights

Nov 10 - Nov 17

$468 → $419

10%

5 nights

Dec 7 - Dec 12

$448 → $400

11%

Popular Airports to fly from Chicago to Punta Cana

Chicago - Punta Cana route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from Chicago to Punta Cana are near the typical level for this route.

📅 Best time to fly

Fly in June for prices as low as $445

Historically, June is the cheapest month to fly, with a median price of $445.

⏱️ Flight duration

Direct flights take 4h 45m

The median flight time for a direct flight to Punta Cana is 4h 45m.

✈️ Airlines & availability

Connecting flights are dominant

Only 6.5% of recent flights from Chicago to Punta Cana are direct.

🏆 Airline highlight

Maersk Air offers direct flights

Maersk Air is one airline that has offered direct flights on this route recently.

🎯 Booking tip

Deals appear frequently

Deals on flights from Chicago to Punta Cana appear frequently, about every 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers flights to Punta Cana, with prices starting from $314, making it a budget-friendly option.

📍 ~25 km from Chicago (reachable by car or train)

💸 Flights from ~$314

Chicago Midway International (MDW)

Chicago Midway International provides another option for flights to Punta Cana, with prices from $435.

📍 ~14 km from Chicago (reachable by car or train)

💸 Flights from ~$435

Chicago Rockford International (RFD)

Chicago Rockford International offers an alternative departure point for flights to Punta Cana, with prices from $431.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$431

Punta Cana main airports to arrive at

Punta Cana International (PUJ)

Cheapest

Punta Cana International Airport is a convenient arrival point for your trip to Punta Cana.

📍 ~5 km from Punta Cana (reachable by car)

💸 Flights from ~$323

Airports nearby Punta Cana used as alternative

La Romana International (LRM)

La Romana International is the closest alternative airport, located within an hour's drive via the Coral Highway.

Punta Cana, Dominican Republic

75% AI deal score

$1,897

$1,518

Save $379

Copa Airlines

Business Class

Frequently Asked Questions About Flights to Punta Cana

Cheap Flights from Chicago to Punta Cana

Today’s best flight deals from Chicago to Punta Cana

Chicago to Punta Cana: Overview

Insights for flights from Chicago to Punta Cana

How much is a round trip from Chicago to Punta Cana

The cheapest time to fly from Chicago to Punta Cana

Direct flights from Chicago to Punta Cana

Last-minute flights going from Chicago to Punta Cana

Biggest price drops on these dates for flights from Chicago to Punta Cana

Popular Airports to fly from Chicago to Punta Cana

Chicago - Punta Cana route insights

Recent fares are near the typical level

Fly in June for prices as low as $445

Direct flights take 4h 45m

Connecting flights are dominant

Maersk Air offers direct flights

Deals appear frequently

Chicago main airports to depart from

Punta Cana main airports to arrive at

Airports nearby Punta Cana used as alternative

Business & First Class Flight Deals to Punta Cana

Best Elite deals to Punta Cana

Oct 28

Oct 31

Oct 28

Oct 28

Oct 30

Oct 30

Oct 27

Oct 29

Oct 31

Oct 28

Dec 07

Oct 28

Frequently Asked Questions About Flights to Punta Cana

When should I buy Chicago to Punta Cana tickets?

What's a cheap fare from Chicago to Punta Cana?

When is the cheapest time of year to fly from Chicago to Punta Cana?

How many flights from Chicago to Punta Cana are non-stop?

How many hours is the flight from Chicago to Punta Cana?

Are there frequently good prices on flights from Chicago to Punta Cana?

Related routes

More routes from Chicago

Flights to Punta Cana from other cities

Chicago to Punta Cana: Overview

Insights for flights from Chicago to Punta Cana

How much is a round trip from Chicago to Punta Cana

The cheapest time to fly from Chicago to Punta Cana

Direct flights from Chicago to Punta Cana

Last-minute flights going from Chicago to Punta Cana

Biggest price drops on these dates for flights from Chicago to Punta Cana

Popular Airports to fly from Chicago to Punta Cana

Chicago - Punta Cana route insights

Recent fares are near the typical level

Fly in June for prices as low as $445

Direct flights take 4h 45m

Connecting flights are dominant

Maersk Air offers direct flights

Deals appear frequently

Chicago main airports to depart from

Punta Cana main airports to arrive at

Airports nearby Punta Cana used as alternative

Business & First Class Flight Deals to Punta Cana

Best Elite deals to Punta Cana

Oct 28

Oct 31

Oct 28

Oct 28

Oct 30

Oct 30

Oct 27

Oct 29

Oct 31

Oct 28

Dec 07

Oct 28

Frequently Asked Questions About Flights to Punta Cana

When should I buy Chicago to Punta Cana tickets?

What's a cheap fare from Chicago to Punta Cana?

When is the cheapest time of year to fly from Chicago to Punta Cana?